CA2000276A1 - Fluorosubstituted benzene derivatives - Google Patents
Fluorosubstituted benzene derivativesInfo
- Publication number
- CA2000276A1 CA2000276A1 CA002000276A CA2000276A CA2000276A1 CA 2000276 A1 CA2000276 A1 CA 2000276A1 CA 002000276 A CA002000276 A CA 002000276A CA 2000276 A CA2000276 A CA 2000276A CA 2000276 A1 CA2000276 A1 CA 2000276A1
- Authority
- CA
- Canada
- Prior art keywords
- mmol
- fluoro
- solution
- acid
- dissolved
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 69
- 125000001153 fluoro group Chemical group F* 0.000 claims description 29
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000007529 inorganic bases Chemical class 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 150000007530 organic bases Chemical class 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- WIFPJDJJFUSIFP-UHFFFAOYSA-N 4-aminobutane-1,2,3-triol Chemical group NCC(O)C(O)CO WIFPJDJJFUSIFP-UHFFFAOYSA-N 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 239000000032 diagnostic agent Substances 0.000 abstract description 9
- 229940039227 diagnostic agent Drugs 0.000 abstract description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 232
- 239000000243 solution Substances 0.000 description 189
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 111
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 99
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 91
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
- 238000004458 analytical method Methods 0.000 description 81
- 229940093499 ethyl acetate Drugs 0.000 description 78
- 235000019439 ethyl acetate Nutrition 0.000 description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 78
- 239000007787 solid Substances 0.000 description 76
- 238000001704 evaporation Methods 0.000 description 68
- 230000008020 evaporation Effects 0.000 description 68
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 65
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
- 239000000706 filtrate Substances 0.000 description 48
- -1 cyclic hydrocarbon radical Chemical class 0.000 description 41
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 31
- 239000002244 precipitate Substances 0.000 description 29
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 28
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 150000001408 amides Chemical class 0.000 description 26
- 230000007717 exclusion Effects 0.000 description 26
- 229910052938 sodium sulfate Inorganic materials 0.000 description 26
- 235000011152 sodium sulphate Nutrition 0.000 description 26
- 239000000126 substance Substances 0.000 description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 24
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 22
- 239000002253 acid Substances 0.000 description 22
- 239000012074 organic phase Substances 0.000 description 21
- 239000000725 suspension Substances 0.000 description 21
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 20
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 150000001768 cations Chemical class 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 17
- MKDRHMDHWIBVRH-UHFFFAOYSA-N 2-amino-1-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanol Chemical compound CC1(C)OCC(C(O)CN)O1 MKDRHMDHWIBVRH-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 150000002500 ions Chemical class 0.000 description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
- 150000003254 radicals Chemical class 0.000 description 13
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 12
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 12
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 11
- 239000005711 Benzoic acid Substances 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 238000007792 addition Methods 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- 125000006239 protecting group Chemical group 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- 150000001450 anions Chemical class 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 210000001519 tissue Anatomy 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- 239000012300 argon atmosphere Substances 0.000 description 8
- 230000037396 body weight Effects 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 7
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 229920001429 chelating resin Polymers 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000003384 imaging method Methods 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- 238000013494 PH determination Methods 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 150000001413 amino acids Chemical class 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 238000003745 diagnosis Methods 0.000 description 6
- 239000002024 ethyl acetate extract Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 6
- 210000003932 urinary bladder Anatomy 0.000 description 6
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 5
- LRCQLCWUUBSUOY-UHFFFAOYSA-N 4-fluoro-2-(trifluoromethyl)aniline Chemical compound NC1=CC=C(F)C=C1C(F)(F)F LRCQLCWUUBSUOY-UHFFFAOYSA-N 0.000 description 5
- SWHGUMZXPAWQQT-UHFFFAOYSA-N 5-[[4-fluoro-2-(trifluoromethyl)phenyl]sulfamoyl]benzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(S(=O)(=O)NC=2C(=CC(F)=CC=2)C(F)(F)F)=C1 SWHGUMZXPAWQQT-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000001555 benzenes Chemical class 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 238000004611 spectroscopical analysis Methods 0.000 description 5
- BJSVKBGQDHUBHZ-UHFFFAOYSA-N 2,4,6-trifluoroaniline Chemical compound NC1=C(F)C=C(F)C=C1F BJSVKBGQDHUBHZ-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- PUHMKDLWHOMHFQ-UHFFFAOYSA-N 5-fluoro-2-phenylmethoxy-3-(2,2,2-trifluoroethylcarbamoyl)benzoic acid Chemical compound OC(=O)C1=CC(F)=CC(C(=O)NCC(F)(F)F)=C1OCC1=CC=CC=C1 PUHMKDLWHOMHFQ-UHFFFAOYSA-N 0.000 description 4
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- QJHFORKOOIYRHX-UHFFFAOYSA-N [2-[5-fluoro-2-hydroxy-3-(2,2,2-trifluoroethylcarbamoyl)anilino]-2-oxoethyl] acetate Chemical compound CC(=O)OCC(=O)NC1=CC(F)=CC(C(=O)NCC(F)(F)F)=C1O QJHFORKOOIYRHX-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- ADYPGMNUYAYGSC-UHFFFAOYSA-N 3-[(2,4,6-trifluorophenyl)sulfamoyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(S(=O)(=O)NC=2C(=CC(F)=CC=2F)F)=C1 ADYPGMNUYAYGSC-UHFFFAOYSA-N 0.000 description 3
- ZNVMTNPNONKLMG-UHFFFAOYSA-N 3-[[4-fluoro-2-(trifluoromethyl)phenyl]sulfamoyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(S(=O)(=O)NC=2C(=CC(F)=CC=2)C(F)(F)F)=C1 ZNVMTNPNONKLMG-UHFFFAOYSA-N 0.000 description 3
- PWAFRMRDUSIXAO-UHFFFAOYSA-N 3-amino-5-fluoro-2-hydroxy-n-(2,2,2-trifluoroethyl)benzamide Chemical compound NC1=CC(F)=CC(C(=O)NCC(F)(F)F)=C1O PWAFRMRDUSIXAO-UHFFFAOYSA-N 0.000 description 3
- PGFQDLOMDIBAPY-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)aniline Chemical compound NC1=CC=C(F)C(C(F)(F)F)=C1 PGFQDLOMDIBAPY-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- DIQKWHVNXKQTOD-UHFFFAOYSA-N ethyl 5-fluoro-2-phenylmethoxy-3-(trifluoromethyl)benzoate Chemical compound CCOC(=O)C1=CC(F)=CC(C(F)(F)F)=C1OCC1=CC=CC=C1 DIQKWHVNXKQTOD-UHFFFAOYSA-N 0.000 description 3
- 230000003834 intracellular effect Effects 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 230000002503 metabolic effect Effects 0.000 description 3
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 3
- YBIPZPBGAGTBGK-UHFFFAOYSA-N methyl 2-chlorosulfonylacetate Chemical compound COC(=O)CS(Cl)(=O)=O YBIPZPBGAGTBGK-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000001139 pH measurement Methods 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 3
- 210000000626 ureter Anatomy 0.000 description 3
- 210000003462 vein Anatomy 0.000 description 3
- CUGDYSSBTWBKII-LXGUWJNJSA-N (2r,3r,4r,5s)-6-(dimethylamino)hexane-1,2,3,4,5-pentol Chemical compound CN(C)C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO CUGDYSSBTWBKII-LXGUWJNJSA-N 0.000 description 2
- SKHROZAEMJEPPI-UHFFFAOYSA-N 1,3-dibromo-5-fluoro-2-phenylmethoxybenzene Chemical compound BrC1=CC(F)=CC(Br)=C1OCC1=CC=CC=C1 SKHROZAEMJEPPI-UHFFFAOYSA-N 0.000 description 2
- JMQZOLVJZAKHML-UHFFFAOYSA-N 1-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-(methylamino)ethanol Chemical compound CNCC(O)C1COC(C)(C)O1 JMQZOLVJZAKHML-UHFFFAOYSA-N 0.000 description 2
- OQSYMTFTJRVOEJ-UHFFFAOYSA-N 1-n,3-n-bis[2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl]-5-[(2,4,6-trifluorophenyl)sulfamoyl]benzene-1,3-dicarboxamide Chemical compound O1C(C)(C)OCC1C(O)CNC(=O)C1=CC(C(=O)NCC(O)C2OC(C)(C)OC2)=CC(S(=O)(=O)NC=2C(=CC(F)=CC=2F)F)=C1 OQSYMTFTJRVOEJ-UHFFFAOYSA-N 0.000 description 2
- CPJSDKYXEWVQLQ-UHFFFAOYSA-N 1-n-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl]-5-fluoro-2-phenylmethoxy-3-n-(2,2,2-trifluoroethyl)benzene-1,3-dicarboxamide Chemical compound O1C(C)(C)OCC1C(O)CNC(=O)C1=CC(F)=CC(C(=O)NCC(F)(F)F)=C1OCC1=CC=CC=C1 CPJSDKYXEWVQLQ-UHFFFAOYSA-N 0.000 description 2
- KIPSRYDSZQRPEA-UHFFFAOYSA-N 2,2,2-trifluoroethanamine Chemical compound NCC(F)(F)F KIPSRYDSZQRPEA-UHFFFAOYSA-N 0.000 description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- PANBQPODRJNUPN-UHFFFAOYSA-N 2-[(2,4-difluorophenyl)sulfamoyl]-n-(2,3,4-trihydroxybutyl)acetamide Chemical compound OCC(O)C(O)CNC(=O)CS(=O)(=O)NC1=CC=C(F)C=C1F PANBQPODRJNUPN-UHFFFAOYSA-N 0.000 description 2
- DCHLMLFZRKHDQP-UHFFFAOYSA-N 2-[[4-fluoro-2-(trifluoromethyl)phenyl]sulfamoyl]acetic acid Chemical compound OC(=O)CS(=O)(=O)NC1=CC=C(F)C=C1C(F)(F)F DCHLMLFZRKHDQP-UHFFFAOYSA-N 0.000 description 2
- OBZYOULNWGJJOT-UHFFFAOYSA-N 2-[[4-fluoro-3-(trifluoromethyl)phenyl]sulfamoyl]acetic acid Chemical compound OC(=O)CS(=O)(=O)NC1=CC=C(F)C(C(F)(F)F)=C1 OBZYOULNWGJJOT-UHFFFAOYSA-N 0.000 description 2
- NFSGHDXTKLVKSD-UHFFFAOYSA-N 2-amino-5-fluorobenzoic acid;hydrochloride Chemical compound Cl.NC1=CC=C(F)C=C1C(O)=O NFSGHDXTKLVKSD-UHFFFAOYSA-N 0.000 description 2
- KZXJVEXPMOPLQG-UHFFFAOYSA-N 2-bromo-4-fluoro-6-(trifluoromethyl)phenol Chemical compound OC1=C(Br)C=C(F)C=C1C(F)(F)F KZXJVEXPMOPLQG-UHFFFAOYSA-N 0.000 description 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 2
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- GFPYVJJWQSZICV-UHFFFAOYSA-N methyl 5-fluoro-2-(trifluoromethylsulfamoyl)benzoate Chemical compound COC(=O)C1=CC(F)=CC=C1S(=O)(=O)NC(F)(F)F GFPYVJJWQSZICV-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- YFMRUVBDKJLPOR-UHFFFAOYSA-N n-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl]-2-[(2,4,6-trifluorophenyl)sulfamoyl]acetamide Chemical compound O1C(C)(C)OCC1C(O)CNC(=O)CS(=O)(=O)NC1=C(F)C=C(F)C=C1F YFMRUVBDKJLPOR-UHFFFAOYSA-N 0.000 description 1
- OGDHKLVEVPLTCA-UHFFFAOYSA-N n-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl]-2-[[4-fluoro-3-(trifluoromethyl)phenyl]sulfamoyl]acetamide Chemical compound O1C(C)(C)OCC1C(O)CNC(=O)CS(=O)(=O)NC1=CC=C(F)C(C(F)(F)F)=C1 OGDHKLVEVPLTCA-UHFFFAOYSA-N 0.000 description 1
- VVVPOZMSZUUCFC-UHFFFAOYSA-N n-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl]-3-[[4-fluoro-2-(trifluoromethyl)phenyl]sulfamoyl]benzamide Chemical compound O1C(C)(C)OCC1C(O)CNC(=O)C1=CC=CC(S(=O)(=O)NC=2C(=CC(F)=CC=2)C(F)(F)F)=C1 VVVPOZMSZUUCFC-UHFFFAOYSA-N 0.000 description 1
- RPDARJDKLZJMEV-UHFFFAOYSA-N n-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl]-5-fluoro-n-methyl-2-(trifluoromethylsulfamoyl)benzamide Chemical compound C=1C(F)=CC=C(S(=O)(=O)NC(F)(F)F)C=1C(=O)N(C)CC(O)C1COC(C)(C)O1 RPDARJDKLZJMEV-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000009206 nuclear medicine Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000005298 paramagnetic effect Effects 0.000 description 1
- 230000009054 pathological process Effects 0.000 description 1
- 229960003330 pentetic acid Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- QVLTXCYWHPZMCA-UHFFFAOYSA-N po4-po4 Chemical compound OP(O)(O)=O.OP(O)(O)=O QVLTXCYWHPZMCA-UHFFFAOYSA-N 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009103 reabsorption Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229940069575 rompun Drugs 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000000264 spin echo pulse sequence Methods 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- QYEFBJRXKKSABU-UHFFFAOYSA-N xylazine hydrochloride Chemical compound Cl.CC1=CC=CC(C)=C1NC1=NCCCS1 QYEFBJRXKKSABU-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/53—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/54—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/60—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having carbon atoms of carboxamide groups, amino groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/09—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton the carbon skeleton being further substituted by at least two halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
- C07C311/39—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/40—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
- C07C65/05—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring o-Hydroxy carboxylic acids
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/84—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving inorganic compounds or pH
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/24—Nuclear magnetic resonance, electron spin resonance or other spin effects or mass spectrometry
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Urology & Nephrology (AREA)
- Molecular Biology (AREA)
- Immunology (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
- Microbiology (AREA)
- Analytical Chemistry (AREA)
- Veterinary Medicine (AREA)
- Biotechnology (AREA)
- Cell Biology (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Radiology & Medical Imaging (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Inorganic Chemistry (AREA)
- Biochemistry (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Materials For Photolithography (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3834704A DE3834704A1 (de) | 1988-10-07 | 1988-10-07 | Fluorsubstituierte benzolderivate |
DEP3834704.0 | 1988-10-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2000276A1 true CA2000276A1 (en) | 1990-04-07 |
Family
ID=6364929
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002000276A Abandoned CA2000276A1 (en) | 1988-10-07 | 1989-10-06 | Fluorosubstituted benzene derivatives |
Country Status (15)
Country | Link |
---|---|
US (1) | US5130119A (xx) |
EP (2) | EP0368429B1 (xx) |
JP (1) | JPH02270832A (xx) |
AT (1) | ATE101392T1 (xx) |
CA (1) | CA2000276A1 (xx) |
DE (2) | DE3834704A1 (xx) |
DK (1) | DK496189A (xx) |
ES (1) | ES2061959T3 (xx) |
FI (1) | FI894714A (xx) |
IE (2) | IE940346L (xx) |
IL (1) | IL91913A0 (xx) |
NO (1) | NO171554C (xx) |
NZ (1) | NZ230945A (xx) |
PT (1) | PT91907B (xx) |
ZA (1) | ZA897640B (xx) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5236694A (en) * | 1990-02-21 | 1993-08-17 | The Board Of Regents, The University Of Texas System | 19f labelled dextrans and antibodies as nmr imaging and spectroscopy agents |
DE4008179A1 (de) * | 1990-03-12 | 1991-09-19 | Schering Ag | Fluorbenzolsulfonamide |
US5318770A (en) * | 1991-10-25 | 1994-06-07 | Mallinckrodt Medical, Inc. | Trifluoromethyl analogs of X-ray contrast media for magnetic resonance imaging |
JPH0797340A (ja) * | 1993-06-03 | 1995-04-11 | Terumo Corp | Mri造影剤組成物 |
US5622687A (en) * | 1994-11-15 | 1997-04-22 | Molecular Biosystems, Inc. | Calixarene conjugates useful as MRI and CT diagnostic imaging agents |
US5491170A (en) * | 1994-12-19 | 1996-02-13 | Warner-Lambert Company | β-carboxy sulfonamide ACAT inhibitors |
DE4447389A1 (de) * | 1994-12-22 | 1996-06-27 | Schering Ag | Disubstituierte p-Fluorbenzolsulfonamide |
US5660815A (en) * | 1995-04-28 | 1997-08-26 | Molecular Biosystems, Inc. | Water soluble fluorinated fatty acid sulfonate derivatives useful as magnetic resonance imaging agents |
US5939451A (en) * | 1996-06-28 | 1999-08-17 | Hoffmann-La Roche Inc. | Use of sulfonamides |
ES2123449B1 (es) | 1997-03-06 | 1999-09-16 | Univ Madrid Nac Educacion | Procedimiento para la obtencion de imagenes y espectros del ph extracelular por resonancia magnetica con indicadores extrinsecos conteniendo 1h o 19f. |
US6963769B1 (en) | 1999-04-21 | 2005-11-08 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Method for enhancing contrast produced by MRI |
US20060183800A1 (en) * | 2004-11-12 | 2006-08-17 | Xianqi Kong | Methods and fluorinated compositions for treating amyloid-related diseases |
JP5445815B2 (ja) * | 2008-02-14 | 2014-03-19 | 日立化成株式会社 | メチロールフェノール化合物、それを用いた樹脂組成物、及び硬化物 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1198301A (en) * | 1966-10-21 | 1970-07-08 | Minnesota Mining & Mfg | Perfluoroalkylsulfonamides |
DK130290B (da) * | 1968-04-08 | 1975-02-03 | Minnesota Mining & Mfg | Fluoralkylsulfonamidosubstituerede arylforbindelser med plantevækstregulerende virkning. |
BE718129A (xx) * | 1968-07-16 | 1969-01-16 | ||
US3920444A (en) * | 1970-12-21 | 1975-11-18 | Minnesota Mining & Mfg | Method comprising the use of N-substituted perfluoroalkyanesulfonamides as herbicidal and plant growth modifying agents, and composition |
FR2550449B1 (fr) * | 1983-08-12 | 1986-01-31 | Commissariat Energie Atomique | Agents de relaxation specifiques d'organes ou de pathologies, utilisables pour modifier les contrastes en imagerie medicale par resonance magnetique nucleaire |
US4766243A (en) * | 1984-08-10 | 1988-08-23 | Occidental Chemical Corporation | Electrophilic fluorination of aromatic compounds |
US4859449A (en) * | 1987-09-14 | 1989-08-22 | Center For Molecular Medicine And Immunology | Modified antibodies for enhanced hepatocyte clearance |
-
1988
- 1988-10-07 DE DE3834704A patent/DE3834704A1/de not_active Withdrawn
-
1989
- 1989-10-04 PT PT91907A patent/PT91907B/pt not_active IP Right Cessation
- 1989-10-05 AT AT89250053T patent/ATE101392T1/de not_active IP Right Cessation
- 1989-10-05 ES ES89250053T patent/ES2061959T3/es not_active Expired - Lifetime
- 1989-10-05 EP EP89250053A patent/EP0368429B1/de not_active Expired - Lifetime
- 1989-10-05 DE DE89250053T patent/DE58906941D1/de not_active Expired - Fee Related
- 1989-10-05 IL IL91913A patent/IL91913A0/xx unknown
- 1989-10-05 EP EP93111849A patent/EP0579261A1/de not_active Withdrawn
- 1989-10-05 FI FI894714A patent/FI894714A/fi not_active Application Discontinuation
- 1989-10-06 JP JP1260326A patent/JPH02270832A/ja active Pending
- 1989-10-06 NO NO894015A patent/NO171554C/no unknown
- 1989-10-06 US US07/417,946 patent/US5130119A/en not_active Expired - Fee Related
- 1989-10-06 ZA ZA897640A patent/ZA897640B/xx unknown
- 1989-10-06 CA CA002000276A patent/CA2000276A1/en not_active Abandoned
- 1989-10-06 DK DK496189A patent/DK496189A/da not_active Application Discontinuation
- 1989-10-09 IE IE940346A patent/IE940346L/xx unknown
- 1989-10-09 NZ NZ230945A patent/NZ230945A/en unknown
- 1989-10-09 IE IE324389A patent/IE64779B1/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
PT91907B (pt) | 1995-05-31 |
AU4269389A (en) | 1990-06-21 |
NO894015D0 (no) | 1989-10-06 |
NO894015L (no) | 1990-04-09 |
DK496189A (da) | 1990-04-08 |
NO171554C (no) | 1993-03-31 |
DE3834704A1 (de) | 1990-06-07 |
AU633850B2 (en) | 1993-02-11 |
IL91913A0 (en) | 1990-06-10 |
US5130119A (en) | 1992-07-14 |
EP0368429A3 (en) | 1990-09-19 |
ZA897640B (en) | 1990-08-29 |
FI894714A (fi) | 1990-04-08 |
DE58906941D1 (de) | 1994-03-24 |
JPH02270832A (ja) | 1990-11-05 |
IE64779B1 (en) | 1995-09-06 |
NO171554B (no) | 1992-12-21 |
FI894714A0 (fi) | 1989-10-05 |
EP0579261A1 (de) | 1994-01-19 |
ATE101392T1 (de) | 1994-02-15 |
IE940346L (en) | 1990-04-07 |
PT91907A (pt) | 1990-04-30 |
NZ230945A (en) | 1992-05-26 |
EP0368429B1 (de) | 1994-02-09 |
EP0368429A2 (de) | 1990-05-16 |
ES2061959T3 (es) | 1994-12-16 |
IE893243L (en) | 1990-04-07 |
DK496189D0 (da) | 1989-10-06 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
FZDE | Discontinued |